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@KNS: we did the same last time. You can also directly compare new car offers so we decided the car we wanted, reached out to like 30 dealers in the greater Boston area to see who could give the best all-in price for what we wanted, and then went back to the lowest three to see if any would go lower. My husband did it all by email and we never had to haggle in person - just walked in and signed!
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@periwinklebee: We have bought our last three cars through car rental agencies, and loved it. about 30-40K miles, about 2-3 years old, only about $11K in price, great condition. We did Hertz for all three I THINK but only 90% positive.
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@Foodnerd81: I wish my husband would take care of all the details, hah hah jealous!
I love him, but he is not a details kind of person.... @KNS: @skiierchck99: Thank you, super helpful! It's especially great to hear that much of the shopping around can be done via email, as it's just super tough to have the time to go around to a bunch of places in person...
@DesertDreams88: Thank you, super good to hear this worked well for you too! I think ideal for me would be to find something not too expensive - that way if we don't use it a ton once our childcare situation changes again or our needs change (not unlikely since job situations/commute and family size could change further in the future), we don't feel like we've sunk a massive amount into a car that we then need to stick with...
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@periwinklebee: One of the big advantages of buying a used car is that if your needs change, or you end up not liking the car, you can resell it for just a bit less than what you bought it for. While there is some risk, I have had good luck buying directly from the previous owner, it is so much cheaper than from a dealership. If the car has more issues than expected, you can always sell it and buy a new one. I ran the carfax, and did research on reliable models. I primarily used Consumer Reports to investigate reliability. Most cars nowadays are pretty reliable, especially if you avoid known unreliable models. I actually avoided Hondas and Toyotas, because they hold their value so well I did not feel like I was getting a good deal by buying used.
I would be more worried buying from a rental car agency, the drivers have no incentive to take care of the car.
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@mdf106: Thank you! I will consider this as well! Good point on some brands maintaining value better than others
I love him, but he is not a details kind of person.... 
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